1-CYANO-3-(1H)-1,2-BENZIODOXOLS - STABLE CYANOIODINANES AND EFFICIENT REAGENTS FOR DIRECT N-ALKYL CYANATION OF N,N-DIALKYLARYLAMINES

被引:126
作者
ZHDANKIN, VV
KUEHL, CJ
KRASUTSKY, AP
BOLZ, JT
MISMASH, B
WOODWARD, JK
SIMONSEN, AJ
机构
[1] Chemistry Department, University of Minnesota-Duluth, Duluth
基金
美国国家科学基金会;
关键词
D O I
10.1016/0040-4039(95)01720-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cyanobenziodoxols 2 and 4 can be prepared from benziodoxols 1 or 3 and cyanotrimethylsilane in the form of stable, crystalline compounds. Cyanobenziodoxol 2 reacts with N,N-dimethylarylamines under mild conditions to afford N-(cyanomethyl)-N-methylarylamines 6 in excellent yields.
引用
收藏
页码:7975 / 7978
页数:4
相关论文
共 29 条
[1]   SYNTHESIS AND REACTION OF SUBSTITUTED ARYLALKOXYIODINANES - FORMATION OF STABLE BROMOARYLALKOXY AND ARYLDIALKOXY HETEROCYCLIC-DERIVATIVES OF TRICOORDINATE ORGANOIODINE(III) [J].
AMEY, RL ;
MARTIN, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (11) :1779-1784
[2]  
FELDMAN KS, 1995, 209TH AM CHEM SOC NA
[3]   PALLADIUM(II) AND COPPER(I) COCATALYZED COUPLING OF STEREODEFINED ALKENYL(PHENYL)IODONIUM TRIFLATES AND UNSATURATED TRI-N-BUTYLSTANNANES [J].
HINKLE, RJ ;
POULTER, GT ;
STANG, PJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (24) :11626-11627
[4]  
HINKLE RJ, 1994, SYNTHESIS-STUTTGART, P313
[5]  
KRASUTSKY AP, 1995, IN PRESS SYNLETT
[6]   OXIDATION OF L-PROLINE METHYL-ESTER DERIVATIVES WITH THE IODOSYLBENZENE TRIMETHYLSILYLAZIDE REAGENT COMBINATION [J].
MAGNUS, P ;
HULME, C .
TETRAHEDRON LETTERS, 1994, 35 (44) :8097-8100
[7]   NEW TRIALKYLSILYL ENOL ETHER CHEMISTRY - DIRECT BETA-AZIDO FUNCTIONALIZATION OF TRIISOPROPYLSILYL ENOL ETHERS [J].
MAGNUS, P ;
LACOUR, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (02) :767-769
[8]   NEW TRIALKYLSILYL ENOL ETHER CHEMISTRY - CONJUGATE ADDITIONS WITHOUT THE ENONE [J].
MAGNUS, P ;
LACOUR, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (10) :3993-3994
[9]   ALPHA-AZIDONATION OF AMIDES, CARBAMATES, AND UREAS WITH THE IODOSYLBENZENE/TRIMETHYLSILYL AZIDE REAGENT COMBINATION - N-ACYLIMINIUM ION PRECURSORS [J].
MAGNUS, P ;
HULME, C ;
WEBER, W .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (10) :4501-4502
[10]   NEW TRIALKYLSILYL ENOL ETHER CHEMISTRY - DIRECT 1,2-BIS-AZIDONATION OF TRIISOPROPYLSILYL ENOL ETHERS - AN AZIDO-RADICAL ADDITION PROCESS PROMOTED BY TEMPO [J].
MAGNUS, P ;
ROE, MB ;
HULME, C .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (02) :263-265